HomeAway is the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We're committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together.

Vacation Rentals in Summerland Key: Houses, Cottages & More

Island View is a charming three bedroom estate situated on three tropical landscaped lots that overlook the Atlantic Ocean and provide you with your own private paradise. Boasting expansive ocean views, and a heated oceanfront pool and tiki bar, ...

Beautiful, new home directly on the water, perfect for boating with easy access to Atlantic or Gulf. Boat dock on bayfront & canalside. Amazing sunrises on the private porch deck. New furniture throughout. This home offers a wonderful opportunity ...

Beautiful custom tropical 3BR/3BA home built in 1999. You will enjoy a newly furnished (2012) home with all the amenities. This home has an open floor plan and beautiful hardwood flooring with large French doors from both the living area and the ...

Unique estate property that has it all. Dockage, sandy beach, shopping, scuba diving, off shore fishing, back country tarpon fishing, lobstering and privacy. This newly constructed estate just completed in July 2009 is located on 1 acre adjacent...

Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in Summerland Key! Privacy 6' Walls surround the Villa to allow sunbathing delights!
The Custom Canal Front Dock has Fenders, Cl...

Island Sunrise Resort is a 3 acre estate with two houses to choose from. The whole property is only rented exclusively to the same party of people (Except for Mini-lobster season). Enjoy the 250' dock, pool, spectacular views of distant islands an...

Vacation Rentals in Summerland Key: Houses, Cottages & More

Island View is a charming three bedroom estate situated on three tropical landscaped lots that overlook the Atlantic Ocean and provide you with your own private paradise. Boasting expansive ocean views, and a heated oceanfront pool and tiki bar, ...

Beautiful, new home directly on the water, perfect for boating with easy access to Atlantic or Gulf. Boat dock on bayfront & canalside. Amazing sunrises on the private porch deck. New furniture throughout. This home offers a wonderful opportunity ...

Beautiful custom tropical 3BR/3BA home built in 1999. You will enjoy a newly furnished (2012) home with all the amenities. This home has an open floor plan and beautiful hardwood flooring with large French doors from both the living area and the ...

Unique estate property that has it all. Dockage, sandy beach, shopping, scuba diving, off shore fishing, back country tarpon fishing, lobstering and privacy. This newly constructed estate just completed in July 2009 is located on 1 acre adjacent...

Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in Summerland Key! Privacy 6' Walls surround the Villa to allow sunbathing delights!
The Custom Canal Front Dock has Fenders, Cl...

Island Sunrise Resort is a 3 acre estate with two houses to choose from. The whole property is only rented exclusively to the same party of people (Except for Mini-lobster season). Enjoy the 250' dock, pool, spectacular views of distant islands an...